Share

More than 14 months after his arrest, Ross Ulbricht has been convicted of being the Dread Pirate Roberts, the masked figure who ran the Silk Road's unprecedented online supermarket for drugs. But the man who first created that mask—and in many ways served as Silk Road's mastermind just as much as Ulbricht—remains a mysterious figure, and one who by all appearances walked away unscathed from his involvement in the Silk Road's billion-dollar drug operation.

As Ulbricht's trial unfolded over the last month, one character appeared again and again in the chat logs prosecutors pulled from the laptop seized from Ulbricht at the time of his arrest: a man calling himself Variety Jones, and later, Cimon.

In the past year and a half U.S. law enforcement have arrested Ulbricht, three of his Silk Road staffers and even the administrator of a second Silk Road, but no law enforcement agency has publicly recorded capturing anyone using Jones' pseudonyms. Yet based on Ulbricht's chat logs and secret journal, Jones served as nothing less than Ulbricht's "mentor," advising the Dread Pirate Roberts closely on everything from managing the site's dealers to hiding his money offshore to threatening enemies with real-world violence.

"[He] was the biggest and strongest willed character I had met through the site thus far," Ulbricht wrote in a 2011 journal entry.

He has advised me on many technical aspect[s] of what we are doing, helped me speed up the site and squeeze more out of my current servers. He has helped me better interact with the community around Silk Road, delivering proclamations, handling troublesome characters, running a sale, changing my name, devising rules, and on and on. He also helped me get my head straight regarding legal protection, cover stories, devising a will, finding a successor, and so on. He’s been a real mentor.

To the average Silk Road user, Variety Jones was just a high-volume marijuana seed dealer, who took great pains to please his customers and ship his product the same day as their order. But behind the scenes, Jones may have had some sort of ownership, partnership or investment in the Silk Road. He's not included in the list of salaried staffers found in Ulbricht's accounting files. Yet over the anonymous and encrypted instant messaging system Torchat, he discussed with Ulbricht every inside detail of the market, from the site's sales statistics to its org chart of employees.

When Ulbricht told Jones that he had revealed his Silk Road secret to both a programmer friend and to his ex-girlfriend, it was Jones who came up with Ulbricht's Dread Pirate Roberts nickname. Ulbricht couldn't even remember exactly what role the Dread Pirate Roberts had played in the film The Princess Bride. Jones explained that the Dread Pirate was a handle passed down from person to person, the perfect cover story for creating the illusion that Ulbricht had handed off ownership of the Silk Road if he were ever caught.

"You need to change your name from Admin, to Dread Pirate Roberts," Jones wrote in an early 2012 chat with Ulbricht. He said that he had given the idea 12 hours of serious thought. "Start the legend now...Clear your old trail - to be honest, as tight as you play things, you are the weak link from those two [previous] contacts."

Variety Jones's relationship with Ulbricht had begun in late 2011, when he alerted Ulbricht to a hackable flaw in the site's use of bitcoin and then started advising him on other technical upgrades. "He quickly proved to me that he had value by pointing out a major security hole in the site I was unaware of," Ulbricht wrote in his journal. "We quickly began discussing every aspect of the site as well as future ideas. He convinced me of a server configuration paradigm that gave me the confidence to be the sole server administrator and not work with someone else at all."

Jones remained Ulbricht's closest confidant and problem solver for the next two years of the site's existence. The chat logs between the two that prosecutors used as evidence in Ulbricht's trial extended to more than a thousand pages. Ulbricht asked for Jones' input in tasks as small as editing the text of warnings he sent to misbehaving sellers, or writing the advertisement for Silk Road's annual 4/20 sale. Jones served as a penetration tester, searching out security vulnerabilities in Silk Road code written by its employees. And he even acted as a kind of PR consultant, warning Ulbricht not to speak with a Vice Magazine reporter who asked for an interview. "Nobody has ever regretted not doing an interview; lots of folks have regretted doing one," Jones wrote.

When one of Ulbricht's highest ranking staffers, Digital Alchemy, disappeared, Ulbricht turned to Jones to ensure the wayward admin's loyalty. Jones offered to track him down in the real world. "I can lay my finger on him in weeks, easy. He leaked ... info like a sieve," Jones wrote. "My point is I want to find him, and have a chat - if it's ok with you...Just make sure he's on side, is all." In another case, Ulbricht would later ask Jones to send a "soldier of fortune" to track down a debtor in Canada.

Ulbricht would write in his journal in late 2011 that Jones' "coming onto the scene has reinspired me and given me direction on the SR project."

He has helped me see a larger vision. A brand that people can come to trust and rally behind. Silk Road chat, Silk Road exchange, Silk Road credit union, Silk Road market, Silk Road everything! And it’s been amazing just talking to a guy who is so intelligent and in the same boat as me, to a certain degree at least.

While he quietly advised Ulbricht, Jones was also an outspoken advocate for the Silk Road's ideology on its user forums, with libertarian views as strong as the ones expressed by the Dread Pirate Roberts himself. "I'm here to be involved with what's going to become an unstoppable force that can work to break the ties that governments use to bind us," Jones wrote in one forum conversation. "I'm here to break the back of prohibition, to make the jack-booted thugs from the DEA roll up their tents and sneak off into the night, and to do what I can to ensure a future where 65 year old MS patients aren't shot by SWAT teams during drug raids because they suspect there was a fucking plant growing in the back room."

In another long post, he imagined (after smoking a joint, he admitted) how the Silk Road would appear to his grandson in the year 2450. "The Road spanned the solar system, from the cities of Earth, to the moons of Jupiter and beyond, the Road was more than just a hidden network of vendors and customers, products and shipments," Jones wrote. "The Road was a concept, an idea...The Road was freedom, a way of life."

In his more than 300 posts to the Silk Road forums, Jones revealed few identifying details. He described himself as a marijuana connoisseur ("cannabis is like wine, there are many and varied flavours and aromas") with more than 2,500 strains of seeds in his "seed vault." He said he had ordered from practically every marijuana vendor on the Silk Road. He enjoyed Robert Heinlein and Arthur C. Clarke, and expressed his deep admiration for the applied cryptographer Phil Zimmermann.

As for his location, Jones occasionally hinted in his forum posts that he lived in the United Kingdom. (His spelling of the word "flavours" in the above quote about cannabis bolsters that idea.) But in his private chats with Ulbricht, he alluded to a transient, international life designed to avoid capture by law enforcement. "My clever plan is to travel all the time, be vague about permanent residence," Jones wrote. "I fly my family to a nice place twice a year to meet."

Ulbricht at one point asked for Jones' advice in replicating that offshore life, putting his money in a tax haven and possibly moving to the Caribbean island of Dominica to avoid American feds. Jones advised him to "make sure your plan includes at least two backup locales." Jones added the costs and wait times for citizenship in various island nations. "Dominican Republic, 24 months, 10 grand gets you a citizenship. Bahamas, 4 months, 280 grand," he wrote. "You can never have too many passports...I plan on collecting passports like Pokemon's. Gotta get 'em all!"

At another point, Jones himself brought up the possibility that Ulbricht could be arrested, suggesting—seemingly in all seriousness—that they should have a backup plan to break him out of prison if necessary. "One of the things i'd like us to look at investing in is a helicopter tour company...seriously, with the amount of $ we're generating, I could hire a small country to come get you." Jones wrote. "And remember that one day when your in the exercise yard, I'll be the dude in the helicopter coming in low and fast, I promise."

Ulbricht, of course, never managed to escape to his island paradise hideout. Instead, he was arrested in October of 2013 in the science fiction section of the Glen Park public library in San Francisco. He's spent most of the year and a half since in a Brooklyn jail cell. And after his conviction on charges ranging from narcotics conspiracy and money laundering to a "kingpin" charge usually applied to mafia bosses and drug cartel leaders, he now faces as much as life in prison.

Variety Jones, meanwhile, seems to have escaped the feds' Silk Road crackdown. His prison-breaking helicopter, for the moment, is nowhere in sight.